June moves to Manhattan for a dream job and the perfect company apartment, only to have them disappear in a puff of reality. It seems that her luck has turned when she gets hired at a coffee shop and finds Chloe, a charming, vivacious roommate - but with the morals of a pirate.

Dating is awkward enough, but when you add Chloe into the mix, it grows tenfold, which June learns the hard way when she begrudgingly allows Chloe to set her up. Meanwhile, James decides to teach an acting class but can't seem to escape his Dawson persona.

June is devastated when she receives a wedding invitation addressed to her and her ex-fiance, so in an attempt make her feel better, Chloe gives June a crash course in confidence and fierceness -- but does too good a job.

June struggles to make ends meet and comes up with a creative way to make some extra cash for this month's rent. She decides to mass produce and sell her homemade jam, but when Chloe gets in on the action, she takes it to a whole new level. Meanwhile, James launches his own line of super skinny jeans called none other than 'Beek Jeans,' of course.

Chloe takes it upon herself to teach June to be sexually empowered and to dabble in some casual encounters. However Chloe's own sex life catches up to her, and to James, when their old sex tape leaks out to the public and James freaks out on how this will affect his likeability on "Dancing with the Stars".

Finally feeling like one of the popular kids, June is desperate to keep pace with Chloe and her partying ways. It's not an easy task, especially when Chloe's 'it girl' lifestyle is so legendary that there's even a whole Japanese comic book series based on it! Meanwhile, James loses it when he discovers that Dean Cain's "Dancing with the Stars" dressing room is bigger than his.